


i really like you

by angryboywonder



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Bottom Jack Kline, Castiel is mentioned - Freeform, M/M, Season/Series 13 Spoilers, Top Dean Winchester
Language: English
Status: Completed
Published: 2018-10-10
Updated: 2018-10-10
Packaged: 2019-07-29 03:59:27
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,261
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16256222
Author URL: https://archiveofourown.org/users/angryboywonder/pseuds/angryboywonder
Summary: Jack is determined to make Dean like him.





	i really like you

**Author's Note:**

> this is a WHOLE ASS clusterfuck

Jack was so determined.

 

He spent the last week trying to figure out ways to impress Dean, just to make him _like_ him, but it was tough. Almost all of his plans have been backfiring; he washed the dishes at the bunker, took over laundry duty, searched endlessly for cases, as he’s been watching Sam doing research online, but almost every case he thinks he’s found is just a dud. Dean thinks Jack is just as terrible as he did in the beginning. However, that hasn’t stopped his attempts.

 

Sam told Jack that it’ll all happen with time, that Dean will eventually come around.

 

It’s one morning, Jack is in the kitchen attempting to cook breakfast, and he doesn’t quite have the hang of it. There’s a loud beeping going on, he doesn’t know where it’s coming from, and the bacon is quickly turning black and there’s a smoke rising from the pan. He’s going back and forth, trying to fan off the pan and find that damn beeping.

 

“Jack, what are you doing?” Sam comes to the rescue and he turns off the burner, throwing some doors open to air it out and before Jack knows it, that awful noise has gone away. Cooking isn’t exactly his specialty. It’s another one of those things where, if he’s seen Sam do it, he’s sure he can do it.

 

“I… Wanted to cook you guys breakfast.”

 

“Ha, good job.” Dean tosses in a short, sarcastic comment, leaning against the doorway with his hands in his pockets. Jack almost didn’t catch the sarcasm – his spirits were lifted for nearly two seconds before he caught Sam shooting a look of disapproval and then Jack lets his shoulders sag.

 

“I’m sorry… I just want to do something nice!”

 

“Yeah, and you almost burned the whole frickin’ bunker down.”

 

“Dean!”

 

“What? Sammy, all he had to do was look at the food the wrong way and the whole place could have come crashing down.”

 

“Stop it.”

 

“Alright, be on baby Satan’s side.” Dean threw his hands up in defeat, walking away.

 

Jack wanted to disappear, and Sam could see it right on his face, but all he had to do was reach out and grab onto his arm, lifting his chin with his opposite hand. “He didn’t mean it…”

 

“You always, _always_ say that, Sam. He hates me.”

 

Sam licks his lips, allowing himself to pull back as he crosses his arms, looking around to find his words. “Dean is… Not always the easiest person to get along with. Him and I don’t always see eye to eye, but there is absolutely nothing wrong with you, and he’ll see that. It may not be right now, but he will.”

 

Jack nods slowly, cracking the smallest smile, just for Sam. He quickly cleans up the kitchen before returning to his room, deciding to rest before hitting the drawing board once again.

 

And then after what felt like an entire of day of constantly beating the dead horse, Jack has one last attempt. He talked it over with Sam, and the older man finally suggested bringing Dean one of his favorite things in the whole world – pie. You can’t go wrong with pie! And the man certainly loves it. And not only that, Jack got to roam around their local convenience store with Sam, which was loads of fun, as Sam let Jack pick out some cool Star Wars themed candy.

 

Standing outside of Dean’s bedroom door, Jack knocks, holding onto the small box with a personal sized apple pie inside of it. He even has a napkin and a fork with him.

 

Dean opens the door, beer in hand as almost always, and raises an eyebrow at Jack. “What do you- is that pie?” And it’s then that Jack sees the older man’s face light up completely.

 

“I want you to like me!”

 

Dean’s face goes back to looking unamused and he sets his beer off on his bedside table and begins rubbing his temples. “Jack… I know you’re not the most civilized, but you don’t just tell someone that you want them to like you.”

 

“But… I’m being honest. I do want you to like me.” He takes a deep breath, holding out the pie. “So, I got you this!”

 

Dean’s expression softens, and he takes the pie, putting it beside his drink on the table. “Thank you, Jack. That was really sweet of you.”

 

“You don’t want to kill me anymore?” Jack pipes up, smile reaching from ear to ear.

 

The older man chuckles, shaking his head, “Okay, we really need to work on your socialization skills some more, but-“ Before Dean can actually finish his sentence, Jack is through the doorway and wrapping his arms around him tight in a hug.

 

“Oh, I’m so happy!”

 

”Whoa, easy there, tiger.” The hug is so tight, Dean is nearly breathless, but he can’t help hugging back. He had to have at least acknowledged the effort Jack has been making towards him.

 

“I’m sorry. I’m just really happy. So happy I could... I could kiss you!”

 

“You could kiss me, huh?” Dean raises an eyebrow, still quite amused.

 

Jack might watch too much television. Surprisingly, Sam watches some cheesy movies from time to time, so whatever socialization skills he _does_ learn, probably comes from what he sees in the fictional world.

 

“Yeah!” Jack’s hold remains on Dean’s waist, although much softer now, and that smile hasn’t left his face. Dean can see how the younger man’s gaze goes back and forth between his eyes and his lips, and it’s almost like time stops when he presses their lips together, inexperience showing as he nearly misses.

 

He lets Jack move his lips against his own, allowing him to get used to the feeling. He’s sure Jack hasn’t actually kissed anybody before, so for him to be the first is somewhat exciting. Although, he wouldn’t admit that, since he did tell the kid not long ago that he would kill him if he had the chance.

 

Jack pulls back, breath suddenly shallow, cheeks heated. Dean pulls him closer, enough to give him room to shut and lock his bedroom door, and then he’s pushing Jack against it, smashing their lips together. The younger man lets out a noise of surprise, hands flying up to grab onto the front of Dean’s shirt.

 

Dean takes control of the kiss, biting at his bottom lip, working their tongues together as he runs a hand up and tangles his fingers in Jack’s soft hair. After a moment he pulls back, leaving a trail of kisses up and down his neck, biting and sucking, getting noises out of Jack that he never thought he would hear. He’s moaning, and he wants nothing more to toss him on the bed and devour him.

 

“Tell me you want it.”

 

Jack can’t even think straight right now – this is the most stimulation he’s ever gotten in his life. He didn’t even know he was this attracted to Dean until now. Or maybe he did, and he just didn’t know how to describe the feeling or gave it that much thought. But here, now, he’s sure. His mind doesn’t quite know how to bring the words together, but he bites his own lip, tugging on Dean’s shirt. “Please… Dean, please…” He manages out, his words sounding strangled and he’s shifting against the door, showing how antsy he really is right now.

 

As soon as the words come out, Dean wastes no time pulling him to the bed and pushing him down on it, crawling over him and attacking his neck once again. Jack really, really loves it. His skin is so sensitive, he turns his head to the opposite side to give Dean more access and gasps at the contact.

 

“You like that?”

 

“Y-Yes…” Jack stutters, blinking up at the ceiling with a hum.

 

“Then you’re really going to like what’s next.”

 

Jack’s excited – he’s already hard, been hard, and he’s now feeling like if he’s not touched soon, he might scream. But he lets the older man remove his clothes and before he knows it, they’re being thrown to the floor.

 

“What about you?” He asks shakily, propping himself on his elbows as he watches Dean kiss down his chest, to his stomach.

 

“I’ll get there.” And then he’s gone, grabbing something from his dresser, and Jack whines, throwing his head back impatiently and reaching a hand down to wrap around his own cock. He barely gets to move his hand before Dean is knocking it away, and then Jack is looking up again, innocent eyes wide. “Did I tell you that you could touch yourself?” The younger man shakes his head slowly.

 

Dean says nothing more, just gives a disapproving look as he pops open the cap to the bottle he’s holding, and then he’s slicking up a few fingers. Jack watches him closely – he would be lying if he said he didn’t get a peak at some of the stuff he’s seen on Sam’s laptop. Normally, whenever something provocative is found, Sam will blame it on Castiel, say he’s “exploring” or some type of that nonsense. But Jack has a general idea of what they’re doing now, he just hasn’t had it done to himself, or made it far enough to do some exploring of his own on his own body.

 

The older man starts pressing a finger against Jack’s entrance, massaging the spot so that he can get a feel for what’s happening, giving him time to adjust. “How’s that?” He mutters, keeping an eye on Jack’s facial expressions. Right now, he’s just watching Dean’s hand, biting on his lower lip as he keeps himself propped up on his elbows. His legs are spread, hips raised, and it’s when he realizes it feels good that he slowly rocks his hips, giving the go to Dean to push the finger inside. As soon as he feels that penetration, he gasps.

 

It takes a moment for Dean to actually create some movement, but before he knows it, there’s two fingers inside of Jack, thrusting in and out, scissoring him. It doesn’t take long for Jack to start squirming on the bed and he’s begging for more.

 

Leaning in, Dean kisses the side of Jack’s face, up to his ear, and he’s whispering, “Do you want me inside of you?”

 

Jack’s frantically nodding his head, “Yes, yes, I do…!”

 

Dean pulls his own shirt over his head and tosses it on the floor next to Jack’s clothes, and quickly his pants and boxers are joining. Jack shifts back on the bed, swallowing hard at the sight, and if it’s at all possible, he’s sure his face is redder than it was before. It even feels hotter.

 

He’s sliding a condom over his cock, slicking it up with lube and stroking himself. “Get on your knees.”

 

Jack didn’t question it or think twice. He was on his hands and knees, looking back at Dean as he felt the intrusion of his cock sliding inside of him. He couldn’t keep quiet. It felt so much fuller than having fingers in him, he immediately fell down to his forearms and had his face in a pillow to muffle his screams as soon as Dean actually started moving in and out.

 

“Does that hurt?”

 

Jack shakes his head, unable to find words. He couldn’t explain quite what he was feeling, but it surely wasn’t pain. That wasn’t a thing he typically felt, he realized. He’s not complaining, though.

 

“Can you move faster…?”

 

Dean complied, groaning as he did so, at even a much harder pace. He nearly loses it when Jack starts pressing back against him, trying to move in time with him. He simply grabs him by the hair, holds him close by sliding an around his waist and he slams into him, over and over, getting a loud whimper in response.

 

It’s almost so loud to the point where he has to hold a hand over his mouth, and within a few more thrusts, Jack is spilling onto the mattress under him. Dean doesn’t let go of his face until releases into the condom, groaning under his breath, squeezing his eyes shut. His hips stutter, and he’s slowly rocking to ride it out.

 

Jack places his hands down onto the bed, holding himself up to avoid touching his own mess. He then rolled over after Dean had pulled out, flipping onto his back, panting as he tried to catch his breath. The younger man watched as Dean walked away, disposing of the condom. He almost didn’t even think about how quickly everything escalated from the time he kissed Dean, but he’s happy it worked out this way. He’s confident now that he no longer dislikes him.

 

As soon as Dean comes back to the bed, Jack is up, giving him another kiss, to which Dean returns. “So, you like me now?”

 

“Jack… Yes, you don’t have to keep asking me.” Dean sounds completely worn out, but he’s still smiling.

 

“I have to tell Sam!”

 

“Whoa, buddy – no, you don’t.” His eyes are wide now, shocked, and he puts a hand out to stop Jack.

 

“Why not?”

 

“Because, knowing you, you’re going to mention that we just _did it_ , and Sam doesn’t need to know that.”

 

“Oh… Sorry.”

 

Dean just shakes his head, grinning and he gets up once again, stretching his body. “How about this… We can take a shower and put on Star Wars. How does that sound?”

 

 

 

 

 

 


End file.
